This study sought to enhance, through qualitative methods, an understanding of the factors that influence adolescents' commitments to extracurricular activities over time. Ile obtained semistructured interview data from 41 adolescents who had been highly involved in athletics or the arts since middle childhood. Ic examined their interpretations of the factors that supported or hindered their continued involvement in these activities over the years. Thematic analysis of the interviews revealed that psychological factors, perceptions of the context, and emerging identity all played a role in decisions to remain involved or quit. Perceived competence and peer relationships emerged as important psychological factors, whereas perceptions of challenge and costs and benefits were important contextual influences. We discuss implications of the findings for the implementation of extracurricular programs that support adolescent development.